JP5220978B2 - フルオロアルキル（メタ）アクリレートコポリマーコーティング組成物 - Google Patents
フルオロアルキル（メタ）アクリレートコポリマーコーティング組成物 Download PDFInfo
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- JP5220978B2 JP5220978B2 JP2002521601A JP2002521601A JP5220978B2 JP 5220978 B2 JP5220978 B2 JP 5220978B2 JP 2002521601 A JP2002521601 A JP 2002521601A JP 2002521601 A JP2002521601 A JP 2002521601A JP 5220978 B2 JP5220978 B2 JP 5220978B2
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- 239000008199 coating composition Substances 0.000 title claims description 31
- 125000003709 fluoroalkyl group Chemical group 0.000 title claims description 25
- 229920001577 copolymer Polymers 0.000 title claims description 9
- 238000000576 coating method Methods 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 239000011248 coating agent Substances 0.000 claims abstract description 24
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims description 23
- 239000000314 lubricant Substances 0.000 claims description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 17
- 239000012528 membrane Substances 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 12
- 238000013508 migration Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000010408 film Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000006162 fluoroaliphatic group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000005515 organic divalent group Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 22
- 150000001875 compounds Chemical class 0.000 abstract description 18
- 239000000758 substrate Substances 0.000 abstract description 13
- 239000000178 monomer Substances 0.000 abstract description 8
- 239000007788 liquid Substances 0.000 abstract description 6
- 239000005871 repellent Substances 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000013307 optical fiber Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 19
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VIEHKBXCWMMOOU-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)C(F)(F)F VIEHKBXCWMMOOU-UHFFFAOYSA-N 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 8
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
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- 230000003068 static effect Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- -1 fluoroalkyl acrylates Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 239000003921 oil Substances 0.000 description 5
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- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
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- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 description 3
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 230000001066 destructive effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229920002313 fluoropolymer Polymers 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 3
- 229940104873 methyl perfluorobutyl ether Drugs 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- RSVZYSKAPMBSMY-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)F RSVZYSKAPMBSMY-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 231100000693 bioaccumulation Toxicity 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical class OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
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- 239000004811 fluoropolymer Substances 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical class OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
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- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- PKAHBRRAHOKBPT-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5-decafluoro-6,6-dimethoxycyclohexane Chemical compound COC1(OC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F PKAHBRRAHOKBPT-UHFFFAOYSA-N 0.000 description 1
- HPFWZNWHCWZFBD-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluorobutan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)(F)CF HPFWZNWHCWZFBD-UHFFFAOYSA-N 0.000 description 1
- YYXWJNBPHDUWJP-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)F YYXWJNBPHDUWJP-UHFFFAOYSA-N 0.000 description 1
- LMVLEDTVXAGBJV-UHFFFAOYSA-N 2,2,3,4,4,4-hexafluorobutyl prop-2-enoate Chemical compound FC(F)(F)C(F)C(F)(F)COC(=O)C=C LMVLEDTVXAGBJV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
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- 238000005530 etching Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000004446 fluoropolymer coating Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000011499 joint compound Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 238000001393 microlithography Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
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- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004297 potassium metabisulphite Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
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- 238000002310 reflectometry Methods 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- UZBIRLJMURQVMX-UHFFFAOYSA-J tetrasodium;pyrene-1,3,6,8-tetrasulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C2C(S(=O)(=O)[O-])=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 UZBIRLJMURQVMX-UHFFFAOYSA-J 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/22—Esters containing halogen
- C08F120/24—Esters containing halogen containing perhaloalkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
- C08F20/24—Esters containing halogen containing perhaloalkyl radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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| PCT/US2001/025527 WO2002016517A2 (en) | 2000-08-18 | 2001-08-15 | Fluoroalkyl (meth)acrylate copolymer coating compositions |
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| JP2002521182A Pending JP2004506784A (ja) | 2000-08-18 | 2001-08-16 | 分解可能な非晶質のフルオロケミカルアクリレートポリマー |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8559056B2 (en) | 2009-08-11 | 2013-10-15 | Fuji Xerox Co., Ltd. | Image processing apparatus, image forming apparatus, and computer-readable recording medium |
Families Citing this family (96)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7320829B2 (en) | 1998-03-05 | 2008-01-22 | Omnova Solutions Inc. | Fluorinated polymer and amine resin compositions and products formed therefrom |
| JP3714870B2 (ja) * | 2000-12-28 | 2005-11-09 | セントラル硝子株式会社 | 透明性含フッ素共重合体 |
| US7514263B2 (en) * | 2001-04-02 | 2009-04-07 | 3M Innovative Properties Company | Continuous process for the production of combinatorial libraries of materials |
| ATE276332T1 (de) * | 2001-05-08 | 2004-10-15 | Merck Patent Gmbh | Polymerisierbares flüssigkristallmaterial |
| WO2002092660A2 (en) | 2001-05-14 | 2002-11-21 | Omnova Soltions Inc | Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| US7491491B2 (en) * | 2002-03-12 | 2009-02-17 | Polytechnic Institute Of New York University | Detecting and/or measuring a substance based on a resonance shift of photons orbiting within a microsphere |
| US7078454B2 (en) * | 2002-04-17 | 2006-07-18 | 3M Innovative Properties Company | Repellent fluorochemical compositions |
| US6894105B2 (en) | 2002-07-26 | 2005-05-17 | 3M Innovatives Properties Company | Dyed fluoropolymers |
| US6930184B2 (en) | 2002-07-26 | 2005-08-16 | 3M Innovative Properties Company | Functional fluorescent dyes |
| IL166241A0 (en) | 2002-07-29 | 2006-01-15 | Rigel Pharmaceuticals Inc | Method of treating or preventing autoimmune diseases with 2,4-pyrimidinedinediamine compounds |
| US7157283B2 (en) * | 2002-08-02 | 2007-01-02 | 3M Innovative Properties Company | Continuous process for the production of combinatorial libraries of modified materials |
| US7632916B2 (en) * | 2002-08-02 | 2009-12-15 | 3M Innovative Properties Company | Process to modify polymeric materials and resulting compositions |
| US6903173B2 (en) * | 2002-08-02 | 2005-06-07 | 3M Innovative Properties Co. | Fluorinated polymers |
| US20040043224A1 (en) * | 2002-08-30 | 2004-03-04 | Shmuel Sternberg | Enhanced hydrophobic membranes and methods for making such membranes |
| ES2421139T3 (es) | 2003-07-30 | 2013-08-29 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidindiamina para su uso en el tratamiento o la prevención de enfermedades autoinmunitarias |
| US7501074B2 (en) * | 2004-03-04 | 2009-03-10 | Barbara Haviland Minor | Haloketone refrigerant compositions and uses thereof |
| US6992224B2 (en) * | 2004-05-12 | 2006-01-31 | Honeywell International Inc. | Manufacture of fluorinated alcohols |
| US7074343B2 (en) * | 2004-05-26 | 2006-07-11 | E. I. Du Pont De Nemours And Company | 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone refrigerant compositions comprising a hydrocarbon and uses thereof |
| FR2871898B1 (fr) * | 2004-06-18 | 2006-09-08 | Alcatel Sa | Composant a fibre optique et fibre optique associee |
| ATE540035T1 (de) | 2004-11-24 | 2012-01-15 | Rigel Pharmaceuticals Inc | Spiro-2,4-pyrimidindiamin-verbindungen und ihre verwendungen |
| US7682771B2 (en) | 2004-12-29 | 2010-03-23 | 3M Innovative Properties Company | Compositions containing photosensitive fluorochemical and uses thereof |
| US7160850B2 (en) | 2004-12-30 | 2007-01-09 | 3M Innovative Properties Company | Compositions of monomeric surfactants |
| US7495118B2 (en) | 2004-12-30 | 2009-02-24 | 3M Innovative Properties Company | Compositions containing C4-swallow tail silanes |
| US7776983B2 (en) * | 2004-12-30 | 2010-08-17 | 3M Innovative Properties Company | Fluorochemical polymeric surfactants |
| US7531730B2 (en) * | 2005-02-08 | 2009-05-12 | Phillip Jason Everly | Non-toxic chemical musical instrument string coating and preservative |
| US7576099B2 (en) * | 2005-02-28 | 2009-08-18 | Renovis, Inc. | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
| WO2007061329A1 (fr) * | 2005-11-25 | 2007-05-31 | Pfc-Tec Llc | Procede pour produire un composant filmogene fluore a faible poids moleculaire et composition sur cette base |
| US7385089B2 (en) * | 2005-12-23 | 2008-06-10 | 3M Innovative Properties Company | Fluorochemical ketone compounds and processes for their use |
| KR100838345B1 (ko) * | 2006-02-17 | 2008-06-13 | 에스케이씨하스디스플레이필름(유) | 표면보호용 코팅 조성물 및 이를 이용한 표면보호필름 |
| US7629298B2 (en) | 2006-02-21 | 2009-12-08 | 3M Innovative Properties Company | Sandstone having a modified wettability and a method for modifying the surface energy of sandstone |
| US7951524B2 (en) | 2006-04-28 | 2011-05-31 | International Business Machines Corporation | Self-topcoating photoresist for photolithography |
| US8945808B2 (en) | 2006-04-28 | 2015-02-03 | International Business Machines Corporation | Self-topcoating resist for photolithography |
| US8034532B2 (en) * | 2006-04-28 | 2011-10-11 | International Business Machines Corporation | High contact angle topcoat material and use thereof in lithography process |
| JP2009203247A (ja) * | 2006-06-16 | 2009-09-10 | Asahi Glass Co Ltd | 含フッ素重合体溶液組成物 |
| US7569715B2 (en) | 2006-07-05 | 2009-08-04 | 3M Innovative Properties Company | Compositions containing silanes |
| JP2010516451A (ja) | 2007-01-19 | 2010-05-20 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化界面活性剤及びその使用方法 |
| WO2008118488A1 (en) * | 2007-03-26 | 2008-10-02 | Egene, Inc. | Capillary electrophoresis using clear coated capillary tubes |
| EP2444428B1 (en) | 2007-06-06 | 2013-07-24 | 3M Innovative Properties Company | Fluorinated compositions and surface treatments made therefrom |
| WO2009008512A1 (ja) * | 2007-07-11 | 2009-01-15 | Asahi Glass Company, Limited | 撥水撥油剤組成物の製造方法および物品 |
| US8319095B2 (en) * | 2007-11-27 | 2012-11-27 | Guardian Industries Corp. | Method of making an antireflective silica coating, resulting product, and photovoltaic device comprising same |
| US7923133B2 (en) | 2007-12-21 | 2011-04-12 | 3M Innovative Properties Company | Coatings and methods for particle reduction |
| US8202579B2 (en) | 2008-03-31 | 2012-06-19 | Cooley Group Holdings, Inc. | Water-resistant fabrics and methods of preparation thereof |
| AU2009244574A1 (en) | 2008-05-05 | 2009-11-12 | 3M Innovative Properties Company | Methods for treating hydrocarbon-bearing formations having brine |
| WO2010009182A2 (en) | 2008-07-18 | 2010-01-21 | 3M Innovative Properties Company | Cationic fluorinated polymer compositions and methods for treating hydrocarbon-bearing formations using the same |
| WO2010080353A2 (en) | 2008-12-18 | 2010-07-15 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated phosphate and phosphonate compositions |
| WO2011027877A1 (en) * | 2009-09-01 | 2011-03-10 | Daikin Industries, Ltd. | Water and oil resistant agent for paper, treatment process and paper |
| JP5546184B2 (ja) * | 2009-09-08 | 2014-07-09 | 株式会社ネオス | 含フッ素ノニオン系界面活性剤 |
| US8992733B2 (en) * | 2010-02-15 | 2015-03-31 | Daikin Industries, Ltd. | Water and oil resistant agent for paper and paper treatment process |
| US9290596B2 (en) | 2010-05-27 | 2016-03-22 | The Chemours Company Fc, Llc | Solvent-based fluoropolymer additives and their use in coating compositions |
| US9029452B2 (en) | 2010-05-27 | 2015-05-12 | E I Du Pont De Nemours And Company | Fluoropolymer additive for coatings |
| KR101145439B1 (ko) * | 2010-06-28 | 2012-05-15 | 한국생산기술연구원 | 초발수 표면 및 그 제조방법 |
| JP5826282B2 (ja) | 2010-11-04 | 2015-12-02 | スリーエム イノベイティブ プロパティズ カンパニー | リン含有酸基及びアルコキシシラン基を含むフッ素化組成物 |
| US8742022B2 (en) | 2010-12-20 | 2014-06-03 | 3M Innovative Properties Company | Coating compositions comprising non-ionic surfactant exhibiting reduced fingerprint visibility |
| US9296904B2 (en) | 2010-12-20 | 2016-03-29 | 3M Innovative Properties Company | Coating compositions comprising non-ionic surfactant exhibiting reduced fingerprint visibility |
| EP2655544A4 (en) | 2010-12-21 | 2015-01-14 | 3M Innovative Properties Co | METHOD FOR TREATING HYDROCARBON-BASED FORMATIONS WITH FLUORINATED AMINE |
| CN102153902B (zh) * | 2011-03-11 | 2013-05-29 | 安徽嘉智信诺化工有限公司 | 一种涂料油墨用氟碳抗缩孔流平剂 |
| US20120285645A1 (en) * | 2011-03-29 | 2012-11-15 | Daikin Industries, Ltd. | Water- and oil-resistant agent having a decreased content of vinyl pyrrolidone monomer |
| KR101430806B1 (ko) * | 2011-08-04 | 2014-08-14 | 주식회사 엘지화학 | 불소계 수지 및 이를 포함하는 감광성 수지 조성물 |
| EP2861678B1 (en) | 2012-06-19 | 2017-10-11 | 3M Innovative Properties Company | Coating compositions comprising polymerizable non-ionic surfactant exhibiting reduced fingerprint visibility |
| CN104755562B (zh) | 2012-06-19 | 2017-05-17 | 3M创新有限公司 | 包含低表面能基团和羟基基团的添加剂以及涂料组合物 |
| CN105263973B (zh) | 2012-11-19 | 2019-06-14 | 3M创新有限公司 | 包含氟化聚合物和非氟化聚合物的组合物及其制备和使用方法 |
| US10106724B2 (en) | 2012-11-19 | 2018-10-23 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ionic polymers |
| EP2935373A4 (en) | 2012-12-20 | 2016-07-27 | 3M Innovative Properties Co | COPOLYMERS WITH ULTRAVIOLETT LIGHT-ABSORBENT GROUPS AND FLUOROLPOLYMER COMPOSITIONS THEREWITH |
| JP6632378B2 (ja) | 2012-12-20 | 2020-01-22 | スリーエム イノベイティブ プロパティズ カンパニー | 紫外線吸収基を有するオリゴマーを含むフルオロポリマー組成物 |
| US9988536B2 (en) * | 2013-11-05 | 2018-06-05 | E I Du Pont De Nemours And Company | Compositions for surface treatments |
| US9777170B2 (en) | 2014-02-25 | 2017-10-03 | The Chemours Company Tt, Llc | Fluorinated polymer additives derived using hydrophilic chain transfer agents for architectural coatings |
| CN104926966A (zh) * | 2014-03-19 | 2015-09-23 | 中国科学院上海有机化学研究所 | 一种低能表面涂层用的含氟聚合物及其制备方法 |
| CN106416443B (zh) | 2014-05-28 | 2020-07-07 | 日东电工株式会社 | 金属框体及使用了该金属框体的通气构造 |
| SG10201806476WA (en) | 2014-06-18 | 2018-08-30 | 3M Innovative Properties Co | Light transparent fluoropolymer composition and article |
| US11110689B2 (en) | 2014-06-25 | 2021-09-07 | 3M Innovative Properties Company | Pressure sensitive adhesive composition including ultraviolet light-absorbing oligomer |
| JP6294513B2 (ja) | 2014-06-25 | 2018-03-14 | スリーエム イノベイティブ プロパティズ カンパニー | 少なくとも１つのオリゴマーを含むフルオロポリマー組成物 |
| CN104830192A (zh) * | 2015-04-29 | 2015-08-12 | 广德嘉宝莉化工有限公司 | 一种高耐候性高韧性水性涂料 |
| EP3313906B1 (en) | 2015-06-25 | 2020-08-05 | 3M Innovative Properties Company | Copolymer including ultraviolet light-absorbing group and compositions including the same |
| WO2017131059A1 (ja) * | 2016-01-27 | 2017-08-03 | 株式会社ニッペコ | 異物除去潤滑組成物、異物除去潤滑組成物の塗布部材、及び、異物除去潤滑組成物の使用方法 |
| EP3448923B1 (en) | 2016-04-25 | 2021-03-17 | 3M Innovative Properties Company | Composite particles for curing epoxy resin compositions and curable and cured epoxy resin compositions prepared using the particles |
| US11008466B2 (en) * | 2016-07-08 | 2021-05-18 | Daikin Industries, Ltd. | Curable composition, process for producing same, and article produced therewith |
| JP6753280B2 (ja) | 2016-11-24 | 2020-09-09 | コニカミノルタ株式会社 | 電子写真感光体 |
| EP3336112A1 (en) | 2016-12-19 | 2018-06-20 | 3M Innovative Properties Company | Fluoroalkyl (meth)acrylate polymers and compositions |
| US20200017623A1 (en) | 2017-03-08 | 2020-01-16 | 3M Innovative Properties Company | Blue led cure on demand compositions |
| KR102556198B1 (ko) * | 2017-07-27 | 2023-07-18 | 닛산 가가쿠 가부시키가이샤 | 박리층 형성용 조성물 및 박리층 |
| WO2019028271A1 (en) * | 2017-08-02 | 2019-02-07 | Massachusetts Institute Of Technology | SUSTAINABLE, WATER RESISTANT COATINGS |
| JP2019061003A (ja) * | 2017-09-26 | 2019-04-18 | コニカミノルタ株式会社 | 電子写真感光体及び画像形成装置 |
| US20200283351A1 (en) * | 2017-09-27 | 2020-09-10 | Arkema Inc. | Halogenated heteroalkenyl- and heteroalkyl-functionalized organic compounds and methods for preparing such compounds |
| JP7157307B2 (ja) * | 2018-05-11 | 2022-10-20 | ダイキン工業株式会社 | 撥水撥油剤および繊維製品 |
| US12476052B2 (en) * | 2018-06-21 | 2025-11-18 | KYOCERA AVX Components Corporation | Delamination-resistant solid electrolytic capacitor |
| US20210277274A1 (en) | 2018-07-18 | 2021-09-09 | 3M Innovative Properties Company | Vehicle sensors comprising repellent surface, protective films, repellent coating compositions, and methods |
| WO2020100113A1 (en) | 2018-11-16 | 2020-05-22 | 3M Innovative Properties Company | Composition including solvent and fluorinated polymer and method of treating a hydrocarbon-bearing formation |
| CN113597822B (zh) * | 2019-03-22 | 2025-09-16 | 汉高股份有限及两合公司 | 使电子元件防水的涂层 |
| BE1027888B1 (nl) * | 2019-12-19 | 2021-07-27 | Unilin Bv | Gebruik van een coating materiaal op de randen van decoratieve panelen en werkwijze |
| US20230347296A1 (en) * | 2020-08-18 | 2023-11-02 | Donaldson Company, Inc. | Article including filtration media and fluoropolymer and methods of making and using same |
| US11837415B2 (en) | 2021-01-15 | 2023-12-05 | KYOCERA AVX Components Corpration | Solid electrolytic capacitor |
| US12606661B2 (en) | 2021-02-03 | 2026-04-21 | Donaldson Company, Inc. | Compositions and articles including perfluoropolyether bottlebrush polymers and methods of making and using same |
| KR102571576B1 (ko) * | 2021-05-17 | 2023-08-28 | 이근수 | 불소계 공중합체, 제조 방법, 이를 포함하는 반사방지막 및 응용 |
| CN119954619A (zh) * | 2023-11-07 | 2025-05-09 | 三明市海斯福化工有限责任公司 | 一种氢氟醚化合物及其应用和制备方法 |
| KR20260117062A (ko) * | 2025-01-21 | 2026-07-28 | 주식회사 케이티앤지 | 에어로졸 생성 물품을 수용하는 패키지용 포장재 및 이를 포함하는 패키지 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666797A (en) | 1950-05-26 | 1954-01-19 | Minnesota Mining & Mfg | Fluorinated alcohols and acetate esters |
| US2841573A (en) | 1955-12-29 | 1958-07-01 | Minnesota Mining & Mfg | Fluorocarbon vinyl-type esters and polymers |
| US2803615A (en) | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbon acrylate and methacrylate esters and polymers |
| US3398182A (en) | 1962-06-22 | 1968-08-20 | Minnesota Mining & Mfg | Fluorocarbon urethane compounds |
| US3177187A (en) | 1963-10-28 | 1965-04-06 | Allied Chem | Sym-tetrafluorodichloroisopropyl acrylate compounds and polymers thereof |
| US3341497A (en) | 1966-01-21 | 1967-09-12 | Minnesota Mining & Mfg | Organic solvent soluble perfluorocarbon copolymers |
| US3462296A (en) | 1966-07-22 | 1969-08-19 | Du Pont | Fluorinated oil- and water-repellent copolymer and process for treating fibrous materials with said copolymer |
| DE1595696A1 (de) * | 1966-11-29 | 1970-04-23 | Hoechst Ag | Polymere Acrylsaeure-perfluor-2,3-dimethyl-buthylester als oel- und wasserabweisende UEberzuege |
| US3792128A (en) * | 1969-12-15 | 1974-02-12 | Air Prod & Chem | Fluoropolymer-carboxylated styrene-butadiene functional surface coating compositions |
| US3811933A (en) * | 1969-12-15 | 1974-05-21 | Air Prod & Chem | Oil and grease resistant paper products and process for treating cellulosic materials |
| US3770685A (en) * | 1972-01-24 | 1973-11-06 | Air Prod & Chem | Functional surface coating compositions for cellulosic material |
| GB1413051A (en) | 1972-03-06 | 1975-11-05 | Minnesota Mining & Mfg | Fabric treatment |
| ZA738419B (en) | 1972-11-06 | 1974-09-25 | Christiaens Sa A | New derivatives of 2-aminoindane,the preparation and use thereof |
| US4001305A (en) | 1974-02-04 | 1977-01-04 | Ciba-Geigy Corporation | Rf-glycols containing two perfluoroalkylthio groups and useful compositions therefrom |
| US4029585A (en) | 1975-07-26 | 1977-06-14 | E. I. Du Pont De Nemours And Company | Aqueous dispersions of perfluoroalkyl esters for treating textiles |
| US4264484A (en) | 1979-01-24 | 1981-04-28 | Minnesota Mining And Manufacturing Company | Carpet treatment |
| FR2592055B1 (fr) * | 1985-12-24 | 1988-05-06 | Charbonnages Ste Chimique | Vernis de protection |
| JP2578735B2 (ja) * | 1985-12-24 | 1997-02-05 | ソシエテ シミツク デ シヤルボナ−ジユ エス．ア− | 保護ワニス |
| JP2502059B2 (ja) | 1986-02-05 | 1996-05-29 | 旭硝子株式会社 | 汚れ除去性の高い撥水撥油剤 |
| EP0250996A3 (en) * | 1986-06-21 | 1988-06-01 | Daikin Industries, Limited | Optical fibers |
| JPH01106001A (ja) * | 1987-10-20 | 1989-04-24 | Mitsubishi Rayon Co Ltd | 光フアイバー鞘材用樹脂組成物 |
| US4849291A (en) | 1987-12-02 | 1989-07-18 | Eastman Kodak Company | Magnetic recording element |
| JPH02298384A (ja) * | 1989-05-12 | 1990-12-10 | Mitsubishi Rayon Co Ltd | 塗膜の形成方法 |
| JPH0312269A (ja) * | 1989-06-12 | 1991-01-21 | Mitsubishi Rayon Co Ltd | 塗膜の形成方法 |
| US5410073A (en) | 1989-12-29 | 1995-04-25 | E. I. Du Pont De Nemours And Company | Manufacture of polyfluoro nitrogen containing organic compounds |
| JPH0425569A (ja) * | 1990-05-22 | 1992-01-29 | Mitsubishi Rayon Co Ltd | 紙艶出し加工用塗料組成物 |
| US5223593A (en) | 1991-08-08 | 1993-06-29 | Minnesota Mining And Manufacturing Company | Fluorine containing plastic optical fiber cores |
| US5274159A (en) | 1993-02-18 | 1993-12-28 | Minnesota Mining And Manufacturing Company | Destructable fluorinated alkoxysilane surfactants and repellent coatings derived therefrom |
| US5488142A (en) | 1993-10-04 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Fluorination in tubular reactor system |
| US6037429A (en) | 1995-06-16 | 2000-03-14 | 3M Innovative Properties Company | Water-soluble fluorochemical polymers for use in water and oil repellent masonry treatments |
| US5641844A (en) * | 1995-12-13 | 1997-06-24 | W. L. Gore & Associates, Inc. | Polymers with crystallizable fluoropolymers |
| US5688884A (en) | 1995-08-31 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Polymerization process |
| EP0889092A4 (en) * | 1996-03-22 | 1999-06-23 | Nippon Zeon Co | LIQUID CONTAINING LUBRICANT POLYMER AND TECHNIQUE FOR FORMING LUBRICANT POLYMER FILM |
| US5772817A (en) | 1997-02-10 | 1998-06-30 | Micro Lithography, Inc. | Optical pellicle mounting system |
| US6005137A (en) | 1997-06-10 | 1999-12-21 | 3M Innovative Properties Company | Halogenated acrylates and polymers derived therefrom |
| JPH1143641A (ja) * | 1997-07-29 | 1999-02-16 | Nagoya Gosei Kk | 切り刃用フッ素樹脂コーティング剤 |
| US6197426B1 (en) * | 1998-01-12 | 2001-03-06 | 3M Innovative Properties Company | Fluorochemical copolymer and fluorochemical copolymer compositions useful for imparting repellency properties to a substrate |
| JP4035892B2 (ja) * | 1998-06-05 | 2008-01-23 | 旭硝子株式会社 | コーティング用組成物 |
| US6238798B1 (en) | 1999-02-22 | 2001-05-29 | 3M Innovative Properties Company | Ceramer composition and composite comprising free radically curable fluorochemical component |
| JP4666855B2 (ja) | 1999-07-20 | 2011-04-06 | スリーエム イノベイティブ プロパティズ カンパニー | 消火組成物中でのフッ素化ケトンの使用法 |
| DE60042561D1 (de) | 1999-10-27 | 2009-08-27 | 3M Innovative Properties Co | Fluorochemische sulfonamide tenside |
-
2001
- 2001-08-15 DE DE60118576T patent/DE60118576T2/de not_active Expired - Lifetime
- 2001-08-15 AT AT01962184T patent/ATE322524T1/de not_active IP Right Cessation
- 2001-08-15 KR KR1020037002284A patent/KR100807896B1/ko not_active Expired - Lifetime
- 2001-08-15 EP EP01962184A patent/EP1311637B8/en not_active Expired - Lifetime
- 2001-08-15 JP JP2002521601A patent/JP5220978B2/ja not_active Expired - Lifetime
- 2001-08-15 AU AU2001283381A patent/AU2001283381A1/en not_active Abandoned
- 2001-08-15 WO PCT/US2001/025527 patent/WO2002016517A2/en not_active Ceased
- 2001-08-16 EP EP01962202A patent/EP1326902B1/en not_active Expired - Lifetime
- 2001-08-16 KR KR1020037002285A patent/KR100808711B1/ko not_active Expired - Lifetime
- 2001-08-16 US US09/931,215 patent/US6649719B2/en not_active Expired - Lifetime
- 2001-08-16 JP JP2002521182A patent/JP2004506784A/ja active Pending
- 2001-08-16 AU AU2001283399A patent/AU2001283399A1/en not_active Abandoned
- 2001-08-16 WO PCT/US2001/025626 patent/WO2002016306A2/en not_active Ceased
- 2001-08-16 DE DE60131671T patent/DE60131671T2/de not_active Expired - Lifetime
-
2012
- 2012-08-17 JP JP2012180827A patent/JP2013028807A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8559056B2 (en) | 2009-08-11 | 2013-10-15 | Fuji Xerox Co., Ltd. | Image processing apparatus, image forming apparatus, and computer-readable recording medium |
Also Published As
| Publication number | Publication date |
|---|---|
| US6649719B2 (en) | 2003-11-18 |
| EP1326902B1 (en) | 2007-11-28 |
| KR20030027034A (ko) | 2003-04-03 |
| KR100807896B1 (ko) | 2008-02-27 |
| EP1311637A2 (en) | 2003-05-21 |
| DE60131671T2 (de) | 2008-10-30 |
| KR100808711B1 (ko) | 2008-02-29 |
| WO2002016306A3 (en) | 2003-03-20 |
| WO2002016517A2 (en) | 2002-02-28 |
| DE60131671D1 (en) | 2008-01-10 |
| ATE322524T1 (de) | 2006-04-15 |
| EP1326902A2 (en) | 2003-07-16 |
| JP2004506810A (ja) | 2004-03-04 |
| JP2004506784A (ja) | 2004-03-04 |
| DE60118576T2 (de) | 2006-11-02 |
| KR20030031981A (ko) | 2003-04-23 |
| WO2002016517A3 (en) | 2002-05-23 |
| DE60118576D1 (de) | 2006-05-18 |
| JP2013028807A (ja) | 2013-02-07 |
| WO2002016306A2 (en) | 2002-02-28 |
| US20020042470A1 (en) | 2002-04-11 |
| EP1311637B8 (en) | 2006-06-28 |
| EP1311637B1 (en) | 2006-04-05 |
| AU2001283399A1 (en) | 2002-03-04 |
| AU2001283381A1 (en) | 2002-03-04 |
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